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Is there anything more soul-stirring than the sweet symphony of success? It’s a sentiment Matt Damon knows all too well. This actor knows that the road to greatness isn’t always draped in rose petals. Despite his stellar portrayal of the conflicted mob mole, Colin Sullivan, in Martin Scorsese’s 2006 crime thrillerThe Departed,fortune didn’t exactly roll out the red carpet for Damon when it came to awards season.

In The Departed, Matt Damon plays Colin Sullivan, a mob mole so inept that he’s like a screen door on a submarine.

Ironically, while the film snagged a bevy of accolades, Damon’s heavyweight performance was waved off by major awards shows. Isn’t it a head-scratcher that the actor, often the human embodiment of ‘critical acclaim’, found himself overlooked? It was as if the awards folks were playing a game of hide and seek with his accolades!

Matt Damon’sThe DepartedCharacter Earned Everything But an Award

Matt Damonis a household name, known for his chameleon-like ability to tackle diverse roles with aplomb. Yet, in Martin Scorsese’sThe Departed, the actor trades in his usual suave demeanor for a character so pathetic, that it might just make you pity him—if only briefly. This role is a far cry from the action-packed bravado of his co-stars like Leonardo DiCaprio, Jack Nicholson, and Mark Wahlberg.

Matt Damon Knows What Made Ben Affleck Accept Batman Role and Surprisingly It Wasn’t Just Zack Snyder Directing the Movie

And Damon’s performance is as grating as a cat on a chalkboard. Sullivan is a character you love to hate—if he were any more irritating, he’d need a warning label. He wanted his character to be a walking, talking anti-hero, totally distinct from the cool and collected persona you might expect.

And his best efforts: Damon took inspiration fromJack Nicholson’s performance as Frank Costello. In an interview withFilm Ink, he described his approach:

Matt Damon Knows What Made Ben Affleck Accept Batman Role and Surprisingly It Wasn’t Just Zack Snyder Directing the Movie

I said to Marty, ‘Alright, we’re in this macho world where everyone’s beating each other up and throwing people through walls – and Jack’s a s*xual dynamo – so here’s what I want to do: I want to lose every fight I’m in and I don’t want my d**k to work! I want to take an aggressive run in the other direction.’

DespiteThe Departedbeing a blockbuster hit, as well as nods for Nicholson and Wahlberg in the Best Supporting Actor category, Damon found himself with a big, fat goose egg. The latter didn’t get a single nomination throughout the 2006 awards season. It seems Sullivan got exactly what he deserved—being thoroughly despised—while Damon was left twiddling his thumbs, wondering what he had to do to get a bit of recognition.

Inspired by Jack Nicholson’s Frank Costello, Damon chose to go in the opposite direction, making his character the ultimate underdog.

How Brad Pitt Convinced Matt Damon to JoinThe Departed

When Matt Damon was working withBrad PittinOcean’s 12,little did he know that a casual chat would lead to a golden ticket straight to Hollywood’s elite club.

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The former was minding his own business when Pitt tossed him an offer he couldn’t refuse—an invitation to star in Martin Scorsese’sThe Departed.Damon, who likely thought Pitt was pulling his leg, was floored when he realized it was no joke. The former recounted with a chuckle (viaGQ):

I remember, we were shooting Ocean’s 12, and Brad came up and said, ‘Hey, do you want to be in a Martin Scorsese movie?’ Because Brad, I don’t know if you know, produced that. Brad was going to play either Leo or my role.

Matt Damon Doesn’t Regret Losing an Oscar-Winning Role of Christian Bale For Which The Batman Star Lost 30 Pounds by Starving Himself

Yes, Pitt was dead serious, and so was Scorsese, who had his sights set on Damon as the latter continued:

I can’t remember which one. I guess they had spoken to Marty, and Marty was like, ‘No, I’d like to have Matt.’ I thought Brad was joking. What actor do you ask that question of? You’re like, ‘Shut up, man.’ He’s like, ‘No, I’m actually serious.’ And then he handed me the script, and it was fantastic. I just felt like that was one of the things that fell from the sky. I’ll always be grateful that I had that chance.

Brad Pitt’s casual offer to Matt Damon turned into a golden ticket for the latter to work with Martin Scorsese.

So, there you have it: a stroke of luck wrapped in a surprise script. Damon’s transition from the lighthearted capers ofOcean’s 12to the gritty world ofThe Departedwas like swapping a comfy pair of slippers for a pair of high-stakes roller skates. And boy, did he make the most of it. Damon’s portrayal of Sullivan was nothing short of stellar!

The Departedis just a click away on Amazon Prime Video.

Siddhika Prajapati

Senior Journalist & Content Head

Articles Published :3310

With over 3,300 articles carved into the digital walls of FandomWire, Siddhika Prajapati excels at creating, curating, and elevating engaging stories. She takes pride in giving these stories a home and, of course, she’s got a Google Knowledge Panel to prove it!Whether it’s reviewing the latest drop on Netflix, Amazon Prime, or Apple TV+, or analyzing the cultural echoes of a streaming hit on Paramount+ or Max, Siddhika is always writing three steps ahead of the discourse.

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